Pyridine → 1,9-Di(1-Pyridiniumyl)Nonane With Dibromide Ions

HRID 1036575Notes

Reaction equation

HRID 1036575 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]Br.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[Br-:1].[Br-:1].[CH2:2]([N+:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N+:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 1049PyridineHCID 206771,9-Dibromononane

Product 1

HCID 114081441,9-Di(1-Pyridiniumyl)Nonane With Dibromide IonsYield 87%

Conditions

Temperature
65 °C

Procedure

1,9-Dibromononane (mmol) was added to a solution (30 mL) of dry pyridine, and the solution heated for 24 hours at 65° C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting clear liquid was isolated in a 87% yield. 1H NMR (300 MHz, DMSO-D6) δ 9.17 (2H, d, C2&C6-H), 8.61 (1H, t, C4-H), 8.18 (2H, t, C3&C5-H), 4.63 (2H, t, C′1-CH2), 1.89 (2H, m, C′2-CH2), 1.22 (5H, m, C′3-5-CH2); 13C NMR (75 MHz, DMSO-D6) δ 145.3, 144.5, 127.9, 60.5, 30.7, 28.4, 28.2, 25.3.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washthe product washed five times with dry diethyl ether
  3. customThe resulting clear liquid was isolated in a 87% yield

Sources & evidence

ORD record
ord-c7baf469ad68451abe1e444b23b7e690
Source dataset
uspto-grants-2013_10
Patent number
US08546415B2

Reaction notes

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